Synthesis and antimicrobial activity of some new 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties

Tarik El-Sayed Ali, Azza Mohammed El-Kazak

Abstract


Some new sulfur-nitrogen heterocyclic systems such as 1,3-thiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3-thiazines incorporating acridine and 1,2,3,4-tetrahydroacridine moieties were synthesized via heterocyclization of the key intermediate 4-(acridin-9-yl)-1-(1,2,3,4-tetrahydroacridin-9-ylcarbonyl)thiosemicarbazide. Structures of the new comp-ounds were established by elemental analyses and spectral data. All the products were also screened in vitro for their antimicrobial activity.

1_1_6_11_800


Keyword(s)


Acridine; 1,2,3,4-Tetrahydroacridine; S,N-heterocycles; Antimicrobial Activity

European Journal of Chemistry, 1 (1), (2010), 6-11

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DOI: http://dx.doi.org/10.5155/eurjchem.1.1.6-11.12

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References

[1]. Bouffier, L.; Demeunynck, M.; Milet, A.; Dumy, P. J. Org. Chem. 2004, 69, 8144-8147.
doi:10.1021/jo0487855
PMid:15527309

[2]. Chiron, J.; Galy, J. P. Synthesis 2004, 313-327.
doi:10.1055/s-2003-44379

[3]. Chen, H. Huaxue Yanjiu Yu Yingyong 2000, 12, 164-168.

[4]. Sivan, S.; Tuchman, S.; Lotan, N. Biosystems 2003, 70, 21-33.
doi:10.1016/S0303-2647(03)00039-X

[5]. Flock, S.; Bailly, F.; Bailly, C.; Waring, M. J.; Henichart, J. P.; Colson, P.; Houssier, C. J. Biomol. Struct. Dyn. 1994, 11, 881-886.

[6]. Gooch, B. D.; Beal, P. A. J. Am. Chem. Soc. 2004, 126, 10603-10610.
doi:10.1021/ja047818v
PMid:15327318

[7]. Stefanska, B.; Bontemps-Gracz, M. M.; Antonini, I.; Martelli, S.; Arciemiuk, M.; Piwkowska, A.; Rogacka, D.; Borowski, E. Bioorg. Med. Chem. 2005, 13, 1969-1975.
doi:10.1016/j.bmc.2005.01.023

[8]. Demeunynck, M. Expert Opin. Ther. Patents 2004, 14, 55-70.

[9]. Abdel-Halim, A. M.; Tawfik, A. M.; Ibrahim, S. S.; El-Kazak, A. M. Indian J. Heterocyclic. Chem. 1994, 3, 165-170.

[10]. Chen, Y. L.; Lu, C. M.; Chen, I. L.; Tsao, L. T.; Wang, J. P. J. Med. Chem. 2002, 45, 4689-4694.
doi:10.1021/jm020102v
PMid:12361395

[11]. Chen, Y. L.; Chen, I. L.; Lu, C. M.; Treng, C. C.; Tsao, L. T.; Wang, J. P. Bioorg. Med. Chem. 2003, 11, 3921-3927.
doi:10.1016/S0968-0896(03)00439-5

[12]. Skotnicki, J. S.; Gilman, S. C.; US 851536; Chem.Abstr. 1990, 112, 118672.

[13]. Cai, S.; Li, Q. S.; Borchardt, R. T.; Kuczera, K.; Schowen, R. L. Bioorg. Med. Chem. 2007, 15, 7281-7287.
doi:10.1016/j.bmc.2007.08.029

[14]. Rao, B. M.; Sangaraju, S.; Srinivasu, M. K.; Madhavan, P.; Devi, M. L.; Kumar, P. R.; Candrasekhar, K. B.; Arpitha, Ch.; Balaji, T. S. J. Pharm. Biomed. Anal. 2006, 41, 1146-1151.
doi:10.1016/j.jpba.2006.01.011
PMid:16473490

[15]. Hancu, G.; Gaspar, A.; Gyeresi, A. J. Biochem. Biophys. Methods 2007, 69, 251-259.
doi:10.1016/j.jbbm.2006.02.003
PMid:16563516

[16]. Bajetti, E.; Zilembo, N.; Bichisao, E.; Pozzi, P.; Toffolatti, L. Crit. Rev. Oncol. Hematol. 2000, 33, 137-142.
doi:10.1016/S1040-8428(99)00062-1

[17]. Demirbas, A.; Ceylan, S.; Demirbas, N. J. Heterocycl. Chem. 2007, 44, 1271-1280.
doi:10.1002/jhet.5570440608

[18]. Guirgis, F. K.; Ghanem, M. H.; Abdel-Hay, M. M. Arzneim.-Forsch. 1976, 26, 435-440.
PMid:134717

[19]. Bashir, Y.; Kann, M.; Stradling, J. R. Pulm. Pharmacol. 1990, 3, 151-154.
doi:10.1016/0952-0600(90)90046-L

[20]. Cohen, S. M.; Erturk, E.; Von Esch, A. M.; Crovetti, A. J.; Bryan, G. T. J. Natl. Cancer Inst. 1975, 54, 841-849.

[21]. Patt, W. C.; Hamilton, H. W.; Taylor, M. D.; Ryan, M. J.; Taylor, D. G.; Connolly, C. J. C.; Doherty, A. M.; Klutchko, S. R.; Sircar, I.; Steinbaugh, B. A.; Batley, B. L.; Painchaud, C. A.; Rapundalo, S. T.; Michniewicz, B. M.; Olson, S. C. J. J. Med. Chem. 1992, 35, 2562-2572.
doi:10.1021/jm00092a006
PMid:1635057

[22]. Jaen, J. C.; Wise, L. D.; Caprathe, B. W.; Tecle, H.; Bergmeier, S.; Humblet, C. C.; Heffner, T. G.; Meltzner, L. T.; Pugsley, T. A. J. Med. Chem. 1990, 33, 311-317.
doi:10.1021/jm00163a051
PMid:1967314

[23]. Bell, F. W.; Cantrell, A. S.; Hogberg, M.; Jaskunas, S. R.; Johansson, N. G.; Jordon, C. L.; Kinnick, M. D.; Lind, P.; Morin Jr., J. M.; Noreen, R.; Oberg, B.; Palkowitz, J. A.; Parrish, C. A.; Pranc, P.; Sahlberg, C.; Ternansky, R. J.; Vasileff, R. T.; Vrang, L.; West, S. J.; Zhang, H.; Zhou, X. X. J. Med. Chem. 1995, 38, 4929-4936.
doi:10.1021/jm00025a010
PMid:8523406

[24]. Rudolph, J.; Theis, H.; Hanke, R.; Endermann, R.; Johannsen, L.; Geschke, F. U. J. Med. Chem. 2001, 44, 619-626.
doi:10.1021/jm0010623
PMid:11170652

[25]. Cecchetti, V.; Cruciani, G.; Filipponi, E.; Fravolini, A.; Tabarrini, O.; Xin, T. Bioorg. Med. Chem. 1997, 5, 1339-1344.
doi:10.1016/S0968-0896(97)00084-9

[26]. Kai, H.; Morioka, Y.; Tomida, M.; Takahashi, T.; Hattori, M.; Hanasaki, K.; Koike, K.; Chiba, H.; Shinohara, S.; Kanemasa, T.; Iwamoto, Y.; Takahashi, K.; Yamaguchi, Y.; Baba, T.; Yoshikawa, T.; Takenaka, H. Bioorg. Med. Chem. Lett. 2007, 17, 3925-3929.
doi:10.1016/j.bmcl.2007.04.099

[27]. Ali, T. E. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1717-1726.
doi:10.1080/10426500701313896

[28]. Ali, T. E.; Abdel-Aziz, S. A.; El-Shaaer, H. M.; Hanafy, F. I.; El-Fauomy, A. Z.; Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 2139-2160.
doi:10.1080/10426500701851291

[29]. Ali, T. E.; Ibrahim, M. A.; Abdel-Karim, S. M. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 2358-2392.
doi:10.1080/10426500802473094

[30]. Alberti, A.; Ritiche, B. Org. Synth. 1960, 3, 53-54.

[31]. Kristian, P.; Baletova, E.; Bernat, J.; Imrich, J.; Sedlak, E.; Danihel, I.; Bohm, S.; Pronayova, N.; Klika, K. D.; Pihlaja, K.; Baranova, J. Chem. Pap. 2004, 58, 268-275.

[32]. Popp, F. D. J. Org. Chem. 1962, 27, 2658-2659.
doi:10.1021/jo01054a518

[33]. Kilka, K. D.; Balentova, E.; Bernat, J.; Imrich, J.; Vavrusova, M.; Kleinpeter, E.; Pihlaja, K.; Koch, A. J. Heterocyclic. Chem. 2006, 43, 633-643.
doi:10.1002/jhet.5570430317

[34]. Kilka, K. D.; Imrich, J.; Vilkova, M.; Bernat, J.; Pihlaja, K. J. Heterocyclic. Chem. 2006, 43, 739-743.
doi:10.1002/jhet.5570430331

[35]. Balentova, E.; Imrich, J.; Bernat, J.; Sucha, L.; Vilkova, M.; Pronayova, N.; Kristian, P.; Kilka, K. D. J. Heterocyclic. Chem. 2006, 43, 645-656.
doi:10.1002/jhet.5570430318

[36]. Tomaščiková, J.; Imrich, J.; Danihel, I.; Böhm, S.; Kristian, P.; Pisarčíková, J.; Sabol, M.; Klika, K.D. Molecules 2008, 13, 501-518.
doi:10.3390/molecules13030501

[37]. Liszkiewicz, H. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1402-1409.
doi:10.1080/10426500701648077

[38]. Keshk, E. M.; El-Desoky, S. I.; Hammouda, M. A. A.; Abdel-Rahman, A. H.; Hegazi, A. G. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 183, 1323-1343.
doi:10.1080/10426500701641304

[39]. Junjappa, H.; Ila, H.; Asokan, C.V. Tetrahedron 1990, 46, 5423-5450.
doi:10.1016/S0040-4020(01)87748-6

[40]. Rahman, A. U.; Choudhary, M. I.; Thomsen, W.J. Bioassay Techniques for drug development, 16 the Netherlands: Harwood Academic Publishers 2001.

[41]. Khan, K. M.; Saify, Z. S.; Zeesha, A. K.; Ahmed, M.; Saeed, M.; Schick, M.; Bkohlbau, H.J.; Voelter, W. Arzneim-Forsch/Drug Res. 2000, 50, 915-922.

[42]. Mishra, D.; Patnaik, S.; Rath, C. C.; Dash, S. K.; Mishra, R. K.; Patnaik, U. Indian J. Pharm. Sci. 2002, 64, 256-259.


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